Hydrochloric Acid → (2R,4S)-2-Methyl-4-phenyl-pyrrolidine

HRID 238990Notes

Reaction equation

HRID 238990 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]1[CH3:19])=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[CH3:19][C@@H:9]1[CH2:10][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][NH:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58002924(2R,4S)-2-Methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58002917(2R,4S)-2-Methyl-4-phenyl-pyrrolidineYield 101.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.68 g of (2R,4S)-2-Methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester (6.42 mmol) were dissolved in 40 ml dichloromethane and 19.2 ml (38.56 mmol) 2N HCl in diethylether dropwise added. After stirring at room temperature for 16 h, the solvents were evaporated, the residue was dissolved in water, the pH was adjusted to pH 9 with aqueous sodium hydroxide, and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure to yield 1.05 g of product.

Workup

  1. customthe solvents were evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f66b2fb0a79143c496596a4109559e24
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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